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60+ Weird Questions to Ask a Girl - Discovering Her Darkest Sides

calendarApril 24, 2017
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If you are in search of awkward questions to ask a girl, then you came to the right place. This article will give you a list of awkward questions to ask her.

Awkward questions are those which cause people to feel uncomfortable. They may be related to sex, relationships or any other social topic.

You will find that some of these questions are hot, crazy, intimate, uncomfortable, inappropriate or weird. You will also find that you will be able to ask some of these questions at different stages in your relationship. However, the list also contains questions that you should never ever ask her. It is very important to read the information below each question so that you can get a better understanding of what you can or cannot ask a girl. I know that you will find this information very informative and interesting. Please check them out and learn what to ask girls!


Inappropriate Questions to ask a Girl

1. What's the longest you've gone without a shower?

This is an awkward question to ask any girl. It is a personal question that you can use when you are playing the question-and-answer game with her.

2. Have you ever been arrested?

This is another awkward question that you definitely want to know the answer to. It is very important to know if the people who you are dealing with have any criminal records and the offenses that they have committed.

awkward question to ask a girlSource

3. Have you ever taken drugs or been arrested for drugs?

This is a question that should be asked before you start any form of relationship with a girl. It can be a very touchy subject for many people, but you should not avoid asking it. Knowing the answer to this question could determine how far the relationship goes.

4. Why are you single at this moment?

This is considered an awkward question because you might be digging up her past. But, it is necessary for you to ask it anyway. You need to know exactly why she is single. Maybe she had a nasty breakup because she was with a jerk, or maybe she is just crazy and no one wants to stay in a relationship with her. Whatever the reason is, you should know.

5. Have you ever stolen goods from a store?


This is one of the most uncomfortable questions of all time. Maybe she will not even answer it truthfully, but it is definitely worth a try. It's one of those good questions to ask a girl if you are trying to determine her views on morality. Or, if you don't have a problem with it, it might be one of the good questions to ask when bored.

6. How much do you presently earn?

This is a very embarrassing question that you should avoid. When you ask a question like this, it suggests that you are in it for the money. It is best to wait until she is ready to share that information with you. Girls might ask guys this question too for the same reasons.

7. Why did your last relationship end?

Maybe this is an awkward question for her, but it is very important that you ask anyway. You want to know why her last relationship ended because you want to assess the situation to see if it was her fault, his fault or another person’s fault.

8. How many males have you been involved with so far?

She will find this question uncomfortable to answer. That is for sure!

9. How many dates should a couple go on before having sex?

Awkward or not, you know you want to hear the answer to this one.

10. Which would you choose, love or money?

The reality is that women prefer males who are financially stable. If you ask her this question, she will be left in an awkward position because she will not want to admit that she loves a man for his money. Ask her this question and see what she has to say.

awkward questions to ask your girlfriendSource

11. What is your most embarrassing moment in public?

The answer to this awkward question should be a very interesting one.

12. Have you ever been involved with another girl?

This is a question that you should probably leave for her to discuss when she is ready. If you ask her this question, she will think that she might be acting like a lesbian in your eyes.

13. Are you on your periods?

This is a question that will create an awkward situation. Therefore, it is best to avoid it.

14. Am I the kind of guy that you are looking for?

This question might be awkward for her if she is just getting to know you. Please let her know more about you before you ask her a question like this one.

15. What is your bust size?

A girl will find this question awkward. No ifs, no buts, no maybes. This is one of those weird personal questions that might be best to avoid early on.

16. Will we be sharing the bill?

If it is the first date, then women like it when the men pay. Women will not be pleased with a question like this one.

17. What is the craziest thing that you have ever done in your entire life?

It is better not to share these things sometimes. If she wants to share it with you, then that is good. But the reality is that sometimes it is better to keep these things to one’s self.

18. Have you ever done an HIV test?

This might be an awkward question for her, but it is a very important question that you need to ask.

19. Have you ever had someone pee in your mouth?

This is an awkward and nasty question to ask her. If you are thinking about crazy questions, then this is one of them. This isn't exactly a good question to ask your crush.

20. Have you ever felt stupid on a date?

This is another awkward question to ask any girl or guy. It is one of those funny questions to ask a girl you like.

21. How long did your previous relationship last?

Asking a girl a question like this one will definitely cause her to feel awkward. However, you will have an idea of how long this girl usually stays in relationships.

Awkward Sexual Questions to Ask a Girl

1. Can I kiss you?

This is an awkward question for her to answer. It doesn’t matter if she says yes or no. It is one of those good but silly questions to ask a girl.

awkward sexual questions to ask a girlSource

2. Does size matter to you?

This may be a very uncomfortable question to ask a girl if you are just getting to know each other. You can ask her this question later down in the relationship.

3. What is your favorite sex position?

This is a hot question to ask a girl. Many females will find it awkward.

4. Where is the most romantic place that you would like to have sex?

This is one of those intimate questions that you can ask your girl.

5. What time of the day do you most enjoy having sex?

Another awkward sex question that you can ask your girlfriend.

6. Have you ever taken money for sex?

This is one of those awkward, embarrassing questions. If you are not dating a former prostitute, then this question will embarrass your girl.

7. Have you ever been sexually abused by a friend?

8. Have you ever been sexually abused by a relative?

9. Have you ever been physically abused by a previous partner?

Questions like these are super personal questions. Sometimes, it is very difficult for persons to share these experiences with you. If she does not want to talk about it then please understand.

10. What is the strangest location that you would like to have sex?

This is a hot question to ask a girl that you are in an intimate relationship with.

11. Would you ever have sex in the movie theater?

12. Would you ever have sex in a church?

These are two awkward questions that will have her thinking for a while.

13. Would you masturbate in my presence?

This is an intimate question that will definitely make a girl feel awkward.

14. Have you ever had phone sex?

A lot of girls have never had phone sex, and many of them do not even know what it is. If she doesn’t, then you will get the chance to teach her all about it.

15. When did you lose your virginity?

This is a personal question for many girls. This question can also cause a lot of embarrassment if the girl lost her virginity at an early age.

16. Have you ever used a sex toy?

This is can be an embarrassing question, but it all depend on how long you have been with her.

17. Is your ex-boyfriend’s penis bigger than mine?

Many girls find it very embarrassing to talk about their previous relationship. It is best not to ask her a question like this. Maybe it is something that she doesn’t want to share with you.

18. Have you ever faked it?

I bet you can’t wait to hear the answer to this one. This is one of those random questions that might get a funny response.

19. How long do you think we need to date before we get married?

It is very important to wait until the right time to ask this question.

20. How long do we need to date before we have sex?

This can be a very awkward question. You can ask it at the beginning of the relationship to know exactly what you are getting into.

21. Which role do you usually take on when you are in the bedroom? The dominant or submissive role?

This question might be awkward for her, but if you have been in a relationship with her for a while, then you can ask her about the role that she prefers to take on in the bedroom. Most women prefer to be the submissive but who knows? Maybe that is not the case with her.

22. Do you like to talk naughty things with your partner?

Some females are shy and do not like to talk naughty with their partners. If you really want to know what she likes, then you can go ahead and ask her this one.

super personal questionsSource

23. Have you ever done the 69 position with a guy?

This is a very awkward and intimate question to ask a girl. She may feel shy to disclose this kind of information to you but if you want to know the answer to this question, then go ahead and ask her.

24. Have you ever slept naked?

I bet you want to know the answer to this one. Go ahead and ask her.

25. Do you prefer making love with the lights on or off?

Hot and intimate question to ask your girl.

26. Do you like it rough or gentle?

Another hot and intimate question to ask a girl who you are in a relationship with. If you are on a date for the first time with a girl, then do not ask her this question. She will not take it well, and it would be a very inappropriate question to ask at that time.

27. Do you have any wild sexual fantasies?

Many girls will find it weird or awkward to disclose this information to you, especially if she is just getting to know you. Ask questions like these later in the relationship.

28. Where do you like to be kissed?

This is an awkward question for a girl to answer, but ask her anyway. And when you find the answer to it then be sure to kiss her at that spot time and time again.

29. At what age did you start to masturbate?

This is an extremely awkward question to ask any girl.

30. Do you like watching porn?

Some persons like to watch porn others do not. The only way to know is to ask her.

31. Do you like giving or receiving oral sex?

Another awkward question to ask her, especially if she doesn’t like to do oral.

32. Have you ever had anal sex?

This is a super awkward question to ask her.

33. If you were given the chance, would you have sex with more than one man at the same time?

Sometimes, you need to ask awkward questions like these so that you know the type of person that she is. Knowing the things that she would or would not do will determine the type of person that she is.

34. Which sexual position do you absolutely hate?

This is another awkward question that you can ask her.

35. Have you ever had sex in water? Did you like it?

If she has tried it before or she likes it then that’s more adventure for both or you. This is an awkward question that is worth asking.

36. Have you had sex in a car?

I bet you want to know the answer to this one.

inappropriate questions to ask a girlSource

37. Which size penis do you prefer? Regular or gigantic?

She will find this question to be awkward and embarrassing.

38. What are some of the sounds that you make during sex?

This is a weird question to ask a girl. She will probably feel embarrassed to make those sounds for you.

39. Do you have a vibrator? How often do you use it?

Very awkward question to ask a girl.

40. Have you ever had sexual fantasies about a family member?

This is the most awkward, inappropriate and weird question to ask any girl. It is better not to ask a question like this one.

Read also:

There you have it, a list of 61 of the most awkward questions to ask your girlfriend. I hope that you found these questions very interesting, and that you might have a better idea of what to ask a girl. Thank you for reading!

Find some women's answering questions that men are too afraid to ask in this video:

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